| Identification | Back Directory | [Name]
2'-FLUORO AEA | [CAS]
166100-37-4 | [Synonyms]
AFEA
2'-FLUORO AEA
AEA, 2'-FLUORO
-fluoroethylamide
Arachidonyl-2&rsquo
2'-FLUORO ANANDAMIDE
Arachidonoyl-2&rsquo
ANANDAMIDE, 2'-FLUORO
FLUOROETHYLEICOSATETRAENAMIDE
Arachidonyl-2-fluoroethylamide
ARACHIDONOYL 2'-FLUOROETHYLAMIDE
N-(2-FLUOROETHYL)-5Z,8Z,11Z,14Z-EICOSATETRAENAMIDE
5,8,11,14-Eicosatetraenamide, N-(2-fluoroethyl)-, (5Z,8Z,11Z,14Z)- | [Molecular Formula]
C22H36FNO | [MDL Number]
MFCD02259376 | [MOL File]
166100-37-4.mol | [Molecular Weight]
349.53 |
| Chemical Properties | Back Directory | [Boiling point ]
496.0±45.0 °C(Predicted) | [density ]
0.925±0.06 g/cm3(Predicted) | [solubility ]
DMF: 10 mg/ml; DMSO: 7 mg/ml; Ethanol: 15 mg/ml; Ethanol:PBS (1:1): 8 mg/ml | [pka]
15.24±0.46(Predicted) |
| Hazard Information | Back Directory | [Description]
Arachidonoyl-2'-fluoroethylamide (2-fluoro AEA) is an analog of anandamide in which the alcohol of the ethanolamide group has been removed and replaced with a fluorine atom. This substitution adds considerably increased binding affinity for the CB1 receptor (Kis = 26.7 and 908 nM for CB1 and CB2, respectively). It also contributes additional selectivity, in that binding to CB2 is decreased relative to AEA.1 However, the in vivo activity of 2-fluoro AEA is enhanced much less than the binding affinity, because the analog remains a good substrate for FAAH and is rapidly hydrolyzed by this enzyme. | [Uses]
Arachidonoyl-2'-fluoroethylamide is a CB1 receptor agonist and an analog of Anandamide (A637220), which is an endogenous cannabinoid and TRPV1 receptor agonist. | [in vivo]
Arachidonoyl 2'-fluoroethylamide (0.25% (w/v) 25 μl) induces IOP (intraocular pressure) initially increased and then decreased in rabbit[1]. | Animal Model: | 2.6-3.6 kg normotensive pigmented rabbit[1] | | Dosage: | 25 μl (0.25% (w/v)) | | Administration: | Unilateral ocular administration | | Result: | Induced IOP (intraocular pressure) in the treated eye initially increased and then decreased. |
| [References]
1. Lin, S., Khanolkar, A.D., Fan, P., et al. Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability J. Med. Chem. 41(27),5353-5361(1998). |
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